Raised in a family of five brothers (and one of a set of fraternal twins) hailing from the east of Massachusetts, Gary Cherone began his pursuit of a career in music only after his ambition to become a professional basketball player was brought to an end by an injury to his knee. In 1978 he put together a "classic rock" cover band called Myth; a move towards original material was made with a second line-up of the band the following year. By 1981 the band had evolved into The Dream, a pop-metal act that gained some notoriety by winning the "Basement Tapes" video competition arranged by MTV. After releasing a 6-song EP, in 1985 The Dream was forced to give up its name after it had been bought by a television station (don't you hate it when that happens?). The new name settled upon was Extreme, and under this banner the band launched into an industry career that endured for the next ten years.

In 1989 Extreme released their self-titled debut album though A&M, but it was their 1990 sophomore effort Extreme II: Pornograffitti and its popular singles More Than Words and Hole Hearted that brought them to the top of the charts. By this time the group had drifted towards a more radio-friendly, pop sound, resulting in the predictable sharp rise/steady decline arc in their subsequent popularity: Extreme III: Three Sides to Every Story (1992) was received somewhat less enthusiastically than its predecessor, and Waiting for the Punchline (1995) fared even more poorly. Between these two releases, however, Cherone established himself somewhat as a performer in his own right by earning favorable critical notices for his portryal of Jesus in a 1994 production of Jesus Christ Superstar. By 1996 the singer briefly found himself on his own after Extreme's guitarist Nuno Bettencourt made the decision to leave the band and pursue a solo career.

Later in the year after the demise of Extreme, in what appeared to be the big break of his career, Cherone was chosen to become the third vocalist for arena rock juggernaut Van Halen. Despite the promising beginning suggested by the #1 single Without You, his tenure was to be the shortest and most widely reviled in Van Halen's history, resulting only in the 1998 studio album Van Halen III and an associated world tour -- both severely panned by a large proportion of both critics and fans. By 1999 the vocalist had parted ways the band, his reputation in the industry severly compromised by the experience. Eager to get back to making his own music, Cherone put together Tribe of Judah, a band whose name and material more clearly displayed the religious beliefs hinted at in his Extreme-era songs; the debut album Exit Elvis was released in 2002 on the independent Spitfire label. Collaborative work with some of his brothers was also undertaken during this period.